Water → HCID 67364938, compound

HRID 245706Notes

Reaction equation

HRID 245706 reaction equation
[CH3:1][C:2]1[C:3]2[N:4]([C:8]([N:11]3[CH2:16][CH2:15][N:14]([CH:17]4[CH2:22][CH2:21][N:20]([C:23](=[O:25])[CH3:24])[CH2:19][CH2:18]4)[CH2:13][CH2:12]3)=[N:9][CH:10]=2)[CH:5]=[CH:6][N:7]=1.[Br:26]N1C(=O)CCC1=O.O>ClCCl>[Br:26][C:10]1[N:9]=[C:8]([N:11]2[CH2:12][CH2:13][N:14]([CH:17]3[CH2:22][CH2:21][N:20]([C:23](=[O:25])[CH3:24])[CH2:19][CH2:18]3)[CH2:15][CH2:16]2)[N:4]2[CH:5]=[CH:6][N:7]=[C:2]([CH3:1])[C:3]=12

Participants

5

Reactant 3

HCID 962WaterHCID 67184N-bromobutanimideHCID 67363904HCID 67363904, compound

Product 1

HCID 67364938HCID 67364938, compoundYield 74.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 1-(4-(4-(8-methylimidazo[1,5-a]pyrazin-3-yl)piperazin-1-yl)piperidin-1-yl)ethanone (0.102 mmol, 35 mg) in dichloromethane (1 ml) at room temperature was added N-bromosuccinimide (0.102 mmol, 18.19 mg). After stirring at room temperature for 5 minutes water was added and the mixture extracted three times with dichloromethane. The combined organic extracts were dried over a phase separation filter and concentrated in vacuo to give 1-(4-(4-(1-bromo-8-methylimidazo[1,5-a]pyrazin-3-yl)piperazin-1-yl)piperidin-1-yl)ethanone (32 mg).

Workup

  1. additionwas added
  2. extractionthe mixture extracted three times with dichloromethane
  3. customThe combined organic extracts were dried over a phase separation
  4. filtrationfilter
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-a2a5a566f10d4b82a8c34721dcd44df5
Source dataset
uspto-grants-2014_02
Patent number
US08658794B2

Reaction notes

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